TW201120148A - Chemical toners comprising modified pigments - Google Patents

Abstract

The present invention relates to chemical toner compositions comprising a resin and a polymer modified pigment comprising a pigment having attached at least one polymeric group. The polymer modified pigment comprises the reaction product or combination product of a modified pigment comprising the pigment having attached at least one organic group which comprises at least one first functional group, and at least one polymer comprising at least one second functional group.

Description

201120148 VI. Description of the Invention: TECHNICAL FIELD OF THE INVENTION The present invention relates to a chemically prepared toner composition comprising a polymer-modified pigment.

The present application claims the benefit of U.S. Provisional Patent Application Serial No. 61/269, filed on Jun. [Prior Art] At present, an electrophotographic method and an image forming apparatus are very common. In electrophotography, an image containing an electrostatic field pattern (also referred to as an electr〇 static latent image) having a generally uneven intensity is formed on the insulating surface of the electrophotographic element. The insulating surface typically comprises a photoconductive layer and a conductive substrate. The latent image is then developed or visualized by contacting the electrostatic latent image with the toner composition. Generally, the toner composition contains a resin and a coloring agent (e.g., a pigment). The toner image is then transferred onto a transfer medium (e.g., paper) and fixed thereon by heat and/or pressure. The final step involves removing residual toner from the electrophotographic element. In general, §, the conventional dry toner composition is prepared by combining a 4-component resin with a color former, followed by mechanical abrasion (particle size attriti). The milling process typically results in an uncontrollable breakage of the particles, resulting in a toner composition having an irregular shape and a relatively broad particle size distribution. There is an increasing demand in the industry for the use of lower levels of dry toner per page to produce a toner composition having an improved image of the I49104.doc 201120148 print quality. In order to meet such needs, 'people have been working to improve the dispersibility of the coloring agent in the resin and to reduce the overall particle size of the toner composition. However, since the monthly & amount consumed during milling generally increases exponentially with particle size, current mechanical milling methods are not effective in producing smaller particle size toners. Further, the irregular shape conventional toner particles do not pile up well like b-like particles, resulting in higher toner waste per page. Therefore, various methods have been developed for producing toner particles having a small and/or regular shape. These methods involve the formation of resin particles in the presence of a colorant. The toner produced by the "in situ" method such as (4) is generally referred to as "chemically prepared toner" (CPT) or chemical toner. For example, one method that has been developed is to combine a polymer latex with an aqueous pigment dispersion and agglomerate it to form polymer particles. Another method involves aqueous suspension polymerization of a pigment in a dispersion of at least one of the monomers. Further, the "pigmented pigment" polyester resin dispersion was combined and the fish and water were combined, followed by evaporation of the solvent. Each of these methods produces a smaller particle size toner combination m having a regular shape, for each of these methods, to maintain or improve the toner due to the smaller particles. The dispersibility of the property 'I colorant in the polymer becomes extremely important. In order to provide good dispersibility, a high level of dispersant can be used in the chemical toner method. This may affect the overall performance of the toner composition (especially the viscosity and chargeability of the mixture used to prepare the toner). And/or the moisture sensitivity of the resulting chemical toner) has a negative impact. Other problems have also been discovered. It has been revealed that a modified pigment to which an organic group is attached can be used in a toner combination 149104.doc 201120148:. For example, 'US Patent 6,2iM67 partially discloses a toner set comprising a product of a mixture of resin particles and chargeable modified pigment particles. The red modified shell pigment particles comprise at least one attached to the pigment particles. An organic ionic group and at least one amphiphilic counterion. Further, a toner composition comprising resin fine particles and modified pigment particles having at least one positively chargeable organic group attached thereto is partially disclosed in U.S. Patent No. 5,955,232 and No. 6,54,238. U.S. Patent No. 6,929,889, the disclosure of which is incorporated herein by reference in its entirety the entire entire entire entire entire entire entire entire entire entire entire entire entire entire entire entire portion Or a swell, Sp represents a spacer group and the rim represents an alkenyl group having 50 carbon atoms. The toner address is also disclosed. Further, a toner composition comprising modified particles to which a polymerizable group is attached is partially disclosed in U.S. Patent No. 6,337,358, No. 6,372,82, and 6,664,312. Modified pigments having specific linking groups that can be used in toners, and in particular chemical toners, are also disclosed in U.S. Patent Publication Nos. 2, _12, and No. While the materials disclosed in such patents and publications provide toner compositions having good overall performance, there is still a need in the art for toners having properties that meet the increasingly demanding printing performance, efficiency, and cost requirements of the industry. Especially chemical toners. SUMMARY OF THE INVENTION In one aspect, a chemical toner composition is provided, the composition comprising a resin and a polymer-modified pigment comprising a pigment to which at least one polymeric group is attached, wherein the polymer The modified pigment comprises a reaction product of a modified pigment and at least one polymer of 149104.doc 201120148, the modified pigment comprising a pigment to which at least one organic group is attached, wherein the organic group comprises at least one first functional group The polymer comprises at least one second functional group, wherein the first functional group of the modified pigment reacts with the second functional group of the polymer to form a polymer modified pigment. In some embodiments, the first functional group of the modified pigment is an electrophilic group and the second functional group of the polymer is a nucleophilic group, or the first functional group is a nucleophilic group of the modified pigment and The second functional group of the polymer is an electrophilic group. In another embodiment, the first functional group of the modified pigment is an electrophilic group and the second functional group of the polymer is a nucleophilic group. In another embodiment, the first functional group of the modified pigment is a nucleophilic group and the second functional group of the polymer is an electrophilic group. In another embodiment of the chemical toner composition, the first functional group of the modified pigment and the second functional group of the polymer are independently selected from the group consisting of: a carboxylic acid; an ester; a ruthenium chloride; Gas; hydrazine azide; isocyanate; ketone; aldehyde; anhydride; guanamine; quinone imine; imine; α, Ρ-unsaturated ketone, aldehyde or sulfone, alkyl epoxide; alkyl sulfonate or alkyl sulfate a base compound; an aromatic compound capable of undergoing addition-elimination reaction; an amine; an anthracene; an alcohol; a mercaptan, an anthracene, an anthracene, a diazene; a carbon anion; and a salt or a derivative thereof. In another embodiment of the chemical toner composition, the first functional b group of the modified pigment reacts with the first functional group of the polymer to form an addition-elimination between the modified pigment and the polymer. product. In another embodiment of the chemical toner composition, the first functional group of the modified pigment is an alkyl sulfate group and the second functional group of the polymer is an amine 149104.doc -6 - 201120148 The alkyl ester group can be a (2-sulfatoethyl)-fluorene group. The organic group may be a benzyl-(2-sulfatoethyl)-stone group. In another set of embodiments, the chemical toner composition can include a first functional group of the modified pigment reacting with a second functional group of the polymer to form a condensation product between the pigment/polymer and the polymer. combination. In one embodiment, the first functional group of the modified pigment is an amine group and the second functional group of the polymer is a carboxylic acid group, and the condensation product is a decylamine. In another embodiment, the first functional group of the modified pigment is a carboxylic acid group and the second functional group of the polymer is an amine group, and the condensation product is decylamine. In another embodiment, the first functional group of the modified pigment is an alcohol group and the second functional group of the polymer is a carboxylic acid group, and the condensation product is an ester. In another embodiment, the first s energy of the modified pigment is a carboxylic acid group, the second functional group of the polymer is an alcohol group, and the condensation product is S. In another set of embodiments, the chemical toner composition can include a first functional group, an anionic or an anionizable group of the modified pigment, and a second functional cation or cationizable group of the polymer. A composition of a group, or a cation- or cation-isable group of a modified pigment, and a second functional group of an anion or an anionizable group of the polymer. In yet another embodiment, the first functional group of the modified pigment can be agglomerated and the base of the polymer can be anionized. In another embodiment, the s month t· group of the modified pigment can be anionized and the second functional group of the polymer can be cationized. In the other & example, the first functional group and the polymer of the modified pigment

A Lueneng reaction to form a salt between the negative pigment and the polymer in the slave <" your gold E 丨 t w A, · two. In still another embodiment, the first functional sulfonic acid group or the carboxylic acid 149104.doc 201120148 group and the second functional hydroxyl group of the polymer are chemically tuned. Another example of the composition of the agent t & fan salt. In the other example of the ^, the first official of the modified pigment "b 1 is an amine group and the polymer H can be based on the two bases or the tickic acid group and the salt. In yet another embodiment, the polymer is an amine terminated polymer. In a further embodiment, the polymeric amine caps the polyalkylene oxide. In another embodiment, the polymer resin. In another aspect, a chemical toner composition is provided, the composition comprising a resin and a polymer-modified pigment comprising a pigment to which at least one polymeric group is attached, wherein the polymer-modified pigment And comprising a modified pigment and a combination product with at least one polymer, wherein the modified pigment comprises a pigment to which at least one organic group is attached, the organic group comprising at least one first-functional group. The polymer comprises at least one a second functional group, wherein the first functional group of the modified pigment and the second functional group of the polymer are coordinated to each other to form a ruthenium polymer modified pigment and wherein the first functional group anionic group of the modified pigment And the second functional group of the polymer is a cationizable group, or the first functional group of the modified pigment is a cationizable group and the first g fluorenyl anionic group of the polymer. In yet another embodiment, the first functional group of the modified pigment coordinates with a second functional group of the polymer to form an association ion pair between the modified pigment and the t σ species. In another embodiment, the first functional sulfonate group of the modified pigment and the second functional amine group of the polymer are in a further defined embodiment, the sulfonate group having the formula _s 〇3-M+, where M+ is Na+, K+, Li+, Cs+, Ca+2, Cu+2, Zn+2, Fe+2, Fe+3 or Zr+4 〇 provides chemical chemistry in another aspect a toner composition comprising 149104.doc 201120148 resin and a polymer-modified conjugate comprising at least one polymeric group and a ruthenium of the earthworm, wherein the polymeric group has the formula _χζ_[ Α Α ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ 颜料 颜料 颜料 颜料 颜料The base 'PAO is a poly-oxyalkylene group; and R_, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group. In a more specific embodiment, the X-system (tetra) group. - (10) is a copolymer of ethylene bromide and % oxypropane. In still another embodiment, 2 is nh. It should be understood that the above summary and the following detailed description are merely illustrative and illustrative. Further explanation of the claimed invention is provided. [Embodiment] The present invention relates to a chemical toner composition comprising a polymer-modified pigment. The toner composition of the present invention is a "chemical toner" Or "chemically prepared toner" (CpT), as defined herein, is a toner having a small and/or regular shape. Conventional toner compositions are prepared by: The resin is combined with a color former, followed by pulverization. In contrast, the chemical toner is usually prepared by a method involving formation of toner particles in the presence of a colorant and a solvent such as an aqueous solvent, without using a pulverization step. Since the energy consumed in milling generally increases exponentially with particle size, the current mechanical milling method used to prepare conventional toner compositions does not effectively produce smaller particle size toners. The method results in irregularly shaped particles that do not stack as well as regular shaped particles' resulting in higher toner waste per page. Since the particles are not as in 149104.doc 20112014 The toner composition of the present invention is obtained by using a pulverization step in a toner composition of 8 s. The toner composition of the present invention has a chemical toner having a small and/or regular shape. The resin of the chemical toner of the present invention may be Any of the resins known in the art. Suitable resin materials include, for example, polyamine, polyolefin, polycarbonate, styrene acrylate, styrene methacrylate, styrene butadiene, crosslinked styrene polymer , epoxy resin, polyurethane, vinyl resin (including homopolymer or copolymer of two or more vinyl monomers), polyester and mixtures thereof. In particular, 'resin may include stupid Homopolymers of ethylene and its derivatives and copolymers thereof, such as polystyrene, poly-p-styrene styrene-polystyrene benzene, styrene-p-chlorostyrene copolymer, styrene-vinyl toluene copolymer, Copolymer of styrene with acrylates (eg decyl acrylate, ethyl acrylate, n-butyl acrylate and 2-ethylhexyl acrylate), stupid ethylene and methacrylate (eg methyl methacrylate, hydrazine) Ethyl acrylate, sulfhydryl Copolymer of n-butyl enoate and 2 ethylhexyl methacrylate, copolymer of styrene, acrylate and methacrylate, or copolymer of styrene with other vinyl monomers such as acrylonitrile (styrene·acrylonitrile-ruthenium copolymer); vinyl mercapto ester; butadiene; vinyl mercapto ketone and maleate. The resin may also be a polymethyl methacrylate resin, a polybutyl methacrylate resin, a polyvinyl acetate resin, a polyvinyl butyral resin, a polyacryl resin, a phenol resin, an aliphatic hydrocarbon or an alicyclic hydrocarbon resin, Petroleum resin or gasified paraffin. The resin may also be a polyester resin such as from terephthalic acid (including substituted terephthalic acid), from one to four carbon atoms in the alkoxy group and one to one in the alkane portion. a bis[(transalkyloxy)phenyl]alkane (which may also be a halogen-substituted alkane) of one carbon atom, and 149104.doc • 10-201120148 having 1 to 4 carbons in the alkylene moiety The copolymerization of the atomic alkanediol. Any of these resin types may be used individually or in combination with these or other resins. The resin is typically present between about 60% by weight of the total chemical toner composition and between . In general, it is especially suitable for xerographic toners. The resin produced has a melting point in the range of from about 135 Torr and a glass transition temperature (Tg) of greater than about 60 °C. The chemical toner composition of the present invention also contains a polymer-modified pigment, and the polymer-modified pigment comprises a pigment to which at least one polymerizable group is attached. The pigment of the polymer-modified pigment may be any type of pigment conventionally used by those skilled in the art, such as black pigment or other color pigments, including blue, black, brown, cyan, green, white, purple, purple. Red, red, orange or yellow pigment. Mixtures of different pigments can also be used. Representative examples of black pigments include various carbon blacks (Pigment Black 7), such as channel black, furnace black, and carbon black, and include, for example, trademarks.

Carbon black sold by Regal®, Black Pearls®, Spheron®, Sterling® and Vulcan® (available from Cabot) under the trademark Raven8,

Carbon Black and CD and Series from Statex®, Furnex® and Neotex®

V (available from Columbian Chemicals) and carbon black and CK series (available from Evonik (Degussa) Industries) under the trademarks c〇rax®, • Durax®, Ecorax® and Purex®. Suitable types of color pigments include, for example, anthraquinones, phthalocyanine blues, phthalocyanine greens, diazos, monoazos, dermatins, anthraquinones, heterocyclic yellows (including diarylates). And bisazo condensation pigments), naphthol-AS, quinophthalones and (sulfur) anthracenes. These colors 149104.doc -11- 201120148

The material may be purchased in powder or filter cake form from a variety of sources including BASp Engelhard and Sun Chemical. For example, the color pigment can be a cyan pigment such as Pigment Blue 5, PB, 15:1, K2, 15:3, 15:4, 15:6 or Pigment Blue 6〇; a purplish red pigment such as Pigment Red 122, Pigment Red 170, Pigment Red 177, Pigment Red 185, Pigment Red 187, Pigment Red 2〇2, Pigment Red 238, Pigment Red 269; Purple Pigment, such as Pigment Violet 19 or Pigment Violet 25; Yellow Pigment, such as Pigment Yellow] Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 65, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 128, Pigment Yellow 139, Pigment Yellow 151, Pigment Yellow 155, Pigment Yellow 18〇, Pigment Yellow 185, Pigment Yellow 218, Pigment Yellow 22〇 or Pigment Yellow 221; Orange Pigment, such as Pigment Orange 38 or Pigment Orange 168; or Green Pigment, such as Pigment Green 7 or Pigment Green 36. Examples of other suitable color pigments are described in c〇i〇

Index, 3rd edition (The Society of Dyers and Colourists, 1982). The pigment of the polymer modified pigment may also be a multiphase aggregate containing or containing a carbon phase and a metal phase. Multiphases of Chinese. Heterogeneous aggregates containing a carbon phase and a ruthenium-containing phase may also be considered to be pulverized carbon black aggregates and heterogeneous aggregates containing a carbon phase and a metal-containing phase may be considered to be metal-treated carbon black aggregates. It is only necessary to recognize that in any case, the ruthenium-containing substance and/or the metal-containing substance are in the same phase as the carbon phase. The multiphase aggregates do not represent a mixture of discrete carbon black aggregates and discrete ceria or metal aggregates and are not carbon black coated with dioxide. Conversely, 'multiphase aggregates useful as pigments in the present invention 149104.doc -12· 201120148 include at least one yttrium enriched on the surface or near the surface of the aggregate (but as part of the aggregate) and/or aggregate Or contain metal areas. Thus, the aggregate contains at least two phases, one of which is carbon and the other contains a ruthenium, a metal-containing species, or both. The ruthenium-containing material, which may be part of the aggregate, is not attached to the carbon black aggregate as the ruthenium dioxide coupling agent, but is actually a part of the aggregate as the carbon phase. The metal-treated carbon black contains at least agglomerates of a carbon phase and a metal-containing phase. The metal-containing substance may include a compound containing cobalt, nickel, chromium or iron, which may impart magnetic properties to the toner composition. The metal-containing material phase may be distributed in at least a portion of the aggregate and is an intrinsic portion of the aggregate. The metal treated carbon black may also contain more than one type of metal-containing material phase. In addition, the metal-treated carbon black may also contain a ruthenium-containing material phase. The details of the preparation of such multiphase aggregates are illustrated in U.S. Patent Nos. 5,83, 5,877,238, 5,904,762, 5,948,835, 6, 6, 28, 6, 6,017,980, and 6, 〇57,387. +. The entire contents of these patent applications are hereby incorporated by reference. The ceria-coated carbon product can also be used as a pigment, as described, for example, in PCT Application No. WO 96/37547, issued Nov. 28, 1996, the disclosure of In this article. The pigment of the polymer-modified pigment may also be a pigment which has been oxidized using an oxidizing agent to introduce an ionic group and/or an ionizable group on the surface. The oxidized pigments prepared in this manner have been found to have a relatively high content of oxygen-containing groups on the surface. Oxidizing agents include, but are not limited to, oxygen, ozone, peroxides (such as hydrogen peroxide), persulfates (including sodium persulfate and potassium persulfate), 149104.doc 201120148 hypohalites (eg, sodium sulphate) An oxidizing acid (such as nitric acid) and an oxidizing agent containing a transitional sizing agent (for example, a high chlorate, a tetraoxide, a chromic oxide or a nitric acid may also be a mixture of oxidizing agents, especially a mixture of gaseous oxidizing agents (for example, / oxygen). 0 It is also possible to introduce ionic groups or ionizable groups using other surface modification methods (such as chaosing and continuous brewing). The pigments of the polymer-modified pigments can be measured by nitrogen adsorption method. Depending on the desired B# of the pigment, there is a wide range of BET surface area. For example, the 2' pigment can have a surface area of about 1 〇m2/g "〇〇m2/g (for example, about 2 〇m shouting 250 "^ or about 20 Carbon black from mVg to 100 m2/g). As is known to those skilled in the art, higher surface areas will generally correspond to smaller primary particle sizes. Pigments may also have a variety of primary particle sizes known in the art. For example, pigments Can have between about 5 nm and about 10 〇 nm (including (four) n Primary particle size from m to about 8 〇 _ b im to about 50 nm. For example, if the higher surface area of the color pigment used for the desired application is not readily available, those skilled in the art should also fully appreciate the visual It is necessary to apply conventional pulverization or smashing techniques (such as ball milling or jet milling) to the pigment to reduce the particle size of the pigment. The pigment of the polymer modified pigment can also have a wide range of dibutyl phthalate. Absorption (DBP) value, which is a measure of pigment structure or branching. For example, the pigment may have a DBP value of about 3 〇 mL / 1 〇〇 § to 1 〇〇 mL / i 〇〇 g (including about 40 mL) /100 g to 9〇mL/1〇〇§ or about 5〇mL/i〇〇§ to 8〇mL/i00 g) of carbon black. In addition, the pigment can have a wide range of primary particle sizes, for example about 1〇 Fine to 10〇11111, including about 1511111 to 6〇枷. The polymer-modified pigment of the chemical toner composition of the present invention comprises a reaction product or a combination product of the modified pigment and at least one polymer. 49] 04.doc -14· 201120148 Wenbei pigment contains pigment with at least one organic group attached. The pigment may be any of those described above for the polymer modified pigment. The organic group of the modified pigment comprises at least one levy t* group, and the polymer comprises at least one The second functional group. Each of these orders is discussed in more detail below. The term "reaction product" as used herein means that the polymer modified pigment is reacted with the polymer by the modified pigment (eg via The product obtained by covalent reaction or separation: reaction. The term "combined product" means that the polymer-modified pigment is obtained by combining the modified pigment with a polymer such that the modified pigment and the polymer interact with each other ( For example, the product obtained via association or coordination). This can also lead to other reactions of these components. For example, the polymer-modified pigment may be a reaction product of an m-material and at least one polymer comprising a pigment to which at least one organic group is attached, wherein the organic group: comprises at least one first functional group, The polymer comprises at least one second functional group. For this example, the first functional group of the modified pigment reacts with the second functional group of the polymer, thereby forming a polymer modified pigment. As an additional embodiment, the polymer-modified pigment may be a grouped product of a modified pigment comprising at least one organic group-linked pigment and at least one polymer, wherein the organic group contains at least one first a functional group of the polyfluorene 〇 3 to V second functional groups, wherein the first functional group b group of the modified pigment and the second functional group of the poly-blocking substance are coordinated or associated with each other, thereby forming a polymer Modified pigment. The first functional group of the functional group and the second functional group of the polymer may be any group capable of reacting with each other or interacting with each other + k h 夂 。. For example, the first functional group 149104.doc -15· 201120148 can be a nucleophilic group and the first functional group can be an electrophilic group and vice versa. Thus, for example, a nucleophilic or electrophilic group can be a carboxylic acid, an ester, a helium, a sulfonium, an azide, an isocyanate, a ketone, an aldehyde, an anhydride, a guanamine, a quinone imine, an imine, a a β-unsaturated ketone, an aldehyde or a sulfone, an alkyl group, an epoxide, a non-alkyl ester or an alkyl sulfate (for example, a (2-sulfatoethyl) group), an amine, an anthracene, Alcohol, thiol, hydrazine, hydrazine, triazene, carbon anion, aromatic compound (especially capable of undergoing addition-elimination reaction), or a salt or derivative thereof. Preferably, the first and second functional groups are independently a carboxylic acid group, an acid anhydride group, an amine group (for example, an alkylamine group, including a benzylamine group, a phenylethylamine group, and a stretching group). a strepylamine group or an aminoalkylamine group, such as a -S〇2-ALKl-NH-ALK2-NH2 group, wherein ALK1 and ALK2 are C2-C8 alkylene groups, which may be the same or different), An alkyl sulfate group, or a salt thereof. As a specific example, the first functional group of the modified pigment reacts with the second functional group of the polymer to form an addition-removal product between the modified pigment and the polymer. When the first functional group of the modified pigment is an alkyl sulfate group (for example, a (2-sulfatoethyl)-sulfone group or, more specifically, a phenyl group (2-sulfatoethyl group)- The reaction product can be produced when the sulfone group (as an electrophilic group) and the second functional group of the polymer is an amine group (as a nucleophilic group). As a further specific example, the first functional group of the modified pigment reacts with the second functional group of the polymer to form a condensed product between the modified pigment and the polymer. This reaction product can be produced when the first functional group of the modified pigment is an amine group and the second functional group of the polymer is a carboxylic acid group, and vice versa. Thus, the resulting condensation product will be the guanamine. Alternatively, this product may also be produced when the first functional group is a drunken group and the second functional group of the polymer is a carboxylic acid group of the polymer, 149104.doc •16-201120148, and vice versa. Of course. Therefore, the resulting condensation product will be §. Further, both the first functional group and the second functional group may be an ionic group or an ionizable group. The ionic group can be an anion or a cation and can be associated with oppositely charged counterions (including inorganic or organic counterions) such as H+, Na+, K+, Li+, NH4+, NR/, acetate, N〇3-, s 〇4-2, R〇S03_, OHj CP 'wherein R represents hydrogen or an organic group such as a substituted or unsubstituted aryl group and/or an alkyl group. The ionizable group is a group capable of forming an ionic group in the medium used. Thus, for example, the first functional group can be an anionic or an anionic group and the second functional group can be a cationic or cationizable group, and vice versa. The anionic group is a negatively charged ionic group which can be formed from a group having an ionizable substituent (an anionizable group) capable of forming an anion such as an acidic substituent. It may also be an anion in the salt of the ionizable substituent. Representative examples of suitable anionic groups include <〇〇_, _s〇3·

, -〇S〇3·, -HP〇3·, -OP〇3-2, and _P〇3·2, and representative examples of anionizable groups include _C00H, _s〇3H' _p〇3H2 _R, SH, _R, 〇H and -S〇2NHCOR, wherein R' represents hydrogen or an organic group such as a substituted or unsubstituted aryl group and/or an alkyl group. The cationic group is a positively charged organic ionic group which can be formed from a cleavable:-substituent substituent (cationizable group) capable of forming a cation such as an amide. For example, an alkyl or arylamine can be protonated in an acidic medium to form an ammonium group, wherein R represents an organic group, such as a substituted or unsubstituted aryl group and/or alkane 149104.doc 17 201120148 Base. As a specific example, the first functional group of the modified pigment can be reacted with a second functional group of the polymer to form a salt between the modified pigment and the polymer. The first functional group of the winter-modified pigment is a sulfonic acid group or a carboxylic acid group (as: ion/anionizable group) and the second functional group of the polymer, an amine group (for: cation/cationizable) This group of reaction products can produce this reaction product and vice versa. The resulting salt will be an ammonium salt. As an additional specific embodiment, the first functional group of the modified pigment can be coordinated with the first & functional group of the polymer to form an association ion pair between the modified pigment and the polymer. When the modified pigment has a _-functional anionic group (for example, a sulfonate group having the formula -s〇3-m+) and the second functional group of the polymer is a cationizable group (for example, an amine group) The product can be produced as a combination of A and A. In this formula, M+ can be, for example, Na+, K+, Li+, Cs+, Ca+2, c,

Zn, Fe 2, Fe+3 or Zr+4. Alternatively, the combined product can be produced when the first functional group of the modified pigment is a cationizable group and the second functional group of the polymer is an anionic group. As described above, the modified pigment comprises a pigment to which at least one organic group is attached, wherein the organic group comprises at least one first functional group. Preferably, the organic groups of the modified pigment are directly attached. The modified pigment can be prepared by any method known to those skilled in the art to attach an organic chemical group to the rabbit black. For example, modified pigments can be prepared using the methods described in the following patents: U.S. Patent Nos. 5,554,739, 5,707,432, 5,837, 〇45, 5,851,28, 5,885,335, 5,895,522 , Nos. 5,900,029, 149104.doc • 18· 201120148 =/=48/and M42,643, and PCT publications. The entire disclosure of the specification of 盥 亥 等 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 Other methods of preparing modified pigments include reacting a pigment having a useful functional group with an agent comprising an organic group, for example, as described in, for example, U.S. Patent No. 6,723,783, the entire disclosure of which is incorporated herein by reference. in. The isotactic pigments can be prepared using the methods set forth above in the references. In addition, the modified carbon black containing a linking functional group can also be prepared by the method described in the following: U.S. Patent No. 31,194 and U.S. Patent No. 6,106,075, 2001-0036994 唬, Canadian Patent No. LhU62, European Patent No. i 3, and PCT Publication No. w〇〇4/63289, and N 汕〇5汕〇^·, P〇lym. Sci·, 17 4π, 1992, the entire contents of each of which is incorporated herein by reference. The amount of organogeranium containing at least one first functional group can vary, for example, from the relative reactivity of the first and first functional groups. For example, the total amount of organic groups can be from about 0.01 to about 10 _0 micromolar organic groups per square meter of pigment surface, as measured by nitrogen adsorption (BET method), including, for example, between about 0.5. Micromole/m2 to between about 4.0 micromoles/m2. Additional linking organic groups that do not contain at least one first functional group can also be used. As also mentioned above, the polymer comprises at least one second functional group. A variety of different polymers can be used and thereby form polymeric groups of polymer modified pigments. In particular, the polymer may be a homopolymer, a copolymer, a trimeric 149104.doc -19·201120148 or may contain any repeating unit of any number or arrangement, which includes a random nozzle, a parent polymer, A graft polymer, a block polymer, a hyperbranched or dendritic polymer, a comb polymer, or any combination thereof. The polymer may have an average molecular weight (weight average molecular weight) of not more than about 20 Å. For example. The polymer may have an average molecular weight of no greater than about 15 Å, 〇〇〇 (e.g., no greater than about 100,000, no greater than 5 Å, or no greater than just). The polymer may also have an average molecular weight (weight average molecular weight) of at least about 5 Torr (e.g., at least about 1 Torr, at least 5 Torr, or at least 10, _). In addition, depending on the particular conditions used to prepare the polymer modified pigment, the polymer may be in the form of a liquid, powder or polymer solution. Suitable examples of polymers comprising at least one functional group include polyamines, polyamines, polycarbonates, polyelectrolytes, polyesters, polyethers (e.g., polyalkylene oxides), polyalcohols (e.g., polyhydroxybenzenes and polyvinyls Alcohol), polyimine, sulfur-containing polymer (such as polyphenylene sulfide), acrylic polymer, polyolefin (including those containing halogen (such as polyvinyl chloride and polydiethylene vinylene)), fluorine polymerization , a polyurethane, a polyacid, or a salt or derivative thereof, or any combination thereof. The 4-clay may also be a polyanhydride such as a maleic anhydride polymer. Further, the polymer may be the same as the resin used in the chemical toner of the present invention which has been explained in more detail above. Preferably, the second functional group of the polymer is on one end of the polymer, and therefore, the polymer is preferably a functional end capping polymer. For example, the polymer is preferably an amine terminated polymer such as an amine terminated polyalkylene oxide. Additional examples include polyamines such as polyetheramines and polyaziridines (indenes) or derivatives thereof; extended ethylenimine oligomers (eg, pentaethylhexamine, hydrazine) or derivatives thereof; poly 149104. Doc •20· 201120148 Amidinoamine (PAMAM), such as Starbum 8 amide amine dendrimer; or any combination thereof, each of which includes a terminal amine group. The amount of polymer and modified pigment will depend on a variety of factors, including the type and molecular weight of the polymer, the type of modified pigment, and the relative reactivity of the modified pigment and the functional groups of the polymer. Preferably, the chemical toner combination of the present invention comprises a polymer-modified pigment comprising a weight ratio of the modified pigment to the polymer of between about 1:3 and about 9: (for example, between about The reaction or combination of the polymer with the modified pigment in the case of between 1:1 and about 6:1. More preferably, the weight ratio of modified pigment to polymer is between about 2:1 and about 41. The preferred polymer-modified pigment of the present invention comprises a pigment to which at least one polymeric group is attached, wherein the polymeric group has the formula HfPAOB. In this formula, it is directly attached to the X-based aryl or heteroaryl group of the pigment and is more than (4) an aryl group. The Z system contains a (iv) sub-linking group such as NR' or an anthracene, wherein R. is H, a C1_C18, a dm fluorenyl group, an aryl group, a aryl group or an aryl group. Preferably, 2 bribes. The pA is a polyepoxy group and includes an alkylene oxide group having from W to about 12 carbons (eg, CH2-CH2-〇.^®. -CH(CH3)-CH2-〇-^a] a polymeric group of '-CH2-CH(CH3)-〇- group, even CH2CH2; a group or a combination thereof). Therefore, the PAO can be a copolymer of ethylene bromide and epoxy propylene. The terminal group of the R-based polymer group, such as an anthracene, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group. The polymer modified pigment may be a reaction product or combination of a modified pigment and a polymer, the modified pigment comprising a pigment to which at least one organic group is attached, the organic group comprising at least one 149104.doc - 21 · 201120148 The second month of thiol, and the polymer contains at least _ second functional groups. The pigments and functional groups can be any of those set forth above. The polymer is a polyepoxy burn, such as an amine terminated polyepoxy, which forms a polymeric group of polymer modified pigment. The amount of polymer and modified pigment may also vary as discussed in more detail above. The toner composition of the present invention is a chemically prepared (tetra) toner, also referred to as a chemical toner. Thus, the toner composition has a smooth surface, an average particle size between about 1 micrometer, or both. Smooth Surfaces Toners are substantially free of sharp or mineral-toothed edges, such as those produced by breaking large particles into smaller particles. The shape of the toner composition may be any shape having a smooth surface, but is preferably a shape having no edges or edges, such as a spherical shape or an elliptical shape (including an egg shape or a horse-shaped potato shape). Preferably, the % = shape is from about U to about 3 Q, more preferably from about U to about 2, and most preferably from about 1.2 to about 1.3. The chemical toner group of the present invention comprising a resin and a polymer-modified pigment: is prepared by any method known in the art. Example %, the chemical toner ^ ^ ^ ^ μ method comprises forming agglomerated toner comprising a resin and a pigment modified by a mouthpiece and then adding the mixture to the temperature of the compound Tg, thereby forming a chemical tone Toner. In this method, the toner is usually prepared by combining the aqueous of the polymer-modified pigment; the aqueous emulsion of the resin and at least one aggregating agent. Optional wax can also be added. Suitable for gasification -, multi-continuous _, sulphuric acid II (= (:! such as multi-surfactant, package (four) or sulphuric acid), or include % ionic surfactants', for example, two-compartment benzene 149104.doc -22 - 201120148 Alkyl ammonium chloride, lauryl tri-f-ammonium chloride, alkylbenzyl methyl vaporized money, alkyl benzyl ammonium chloride, benzaik〇nium chlonde, bromine Cetylpyridinium rust, Cl:, c丨5 or c丨7 trimethylammonium bromide, quaternized ammonium polyoxyethylalkylamine salt or dodecylbenzyltriethyl chloride A mixture may be used. The aggregating agent causes the resin to form aggregated particles with the polymer-modified pigment, which may be, for example, from about 1% to about 1% by weight based on the weight of the toner. The amount can be used to change the pH. Therefore, depending on the pigment dispersion and/or the aqueous resin emulsion modified by the polymer, the aggregating agent can be an acid or a test. Alternatively, it can be formed by mechanical or physical methods. Aggregating the toner. The agglomerated toner obtained by this method is then heated to a temperature higher than the Tg of the polymer and kept sufficient to form a chemical toner. The time of the composition. Other details regarding the specific aspects of this method are described in, for example, U.S. Patent Nos. 6,562,541, 6, 5, 3, and 5,977, 21, the entire contents of each of which are incorporated by reference. The method is also incorporated herein. The chemical toner composition of the present invention can also be prepared by a method comprising forming a polymer-modified pigment in at least one monomer to form a dispersion of the dispersion in water. In the medium (especially water), in this method it may be in the polymer modified pigment dispersion or in the formation of aqueous suspension = addition of initiator, but preferably in the polymer modified pigment dispersion The component is selected, for example, a stabilizer. Then, the resulting resin and the polymer-modified pigment are formed: the agent: the monomer can be the above-mentioned chemical toner composition of the present invention. Any of the other details of this method can be found in, for example, U.S. Patent No. 4, 149, 104, doc, 23, 2011, 2014, 6,264, 357, 6, 14, 394, 394, 5, 741, 618. , 5'〇43,404, 4,845,007 and No. 4,601,968, the entire contents of each of which is incorporated herein by reference. The chemical toner composition of the present invention may also be prepared by the method comprising: the polymer modified pigment comprises at least one non- Forming a dispersion in an aqueous solvent and a resin solution of at least one polyester resin to form an aqueous emulsion in an aqueous medium (for example, water), and evaporating the solvent to form a chemical toner. Also dispersed in the modified pigment Other optional components, such as dispersing aids and emulsion stabilizers, may be added to the liquid or after forming the aqueous emulsion. The polyester resin may be one of those used in the preparation of the chemical toner composition as detailed above. Either. Further details regarding the specific aspects of this method can be found in, for example, U.S. Patent No. 6,787,28, and No. 5, No. 7, the entire disclosure of which is incorporated herein by reference. The chemical toner may also be encapsulated in such a method of forming a chemical toner composition. The encapsulation is such that a polymer shell is formed around the toner to produce a chemical toner having a core/shell structure. Any encapsulation method known in the art can be used. The polymer used as the shell is selected: imparting toner properties and handling properties. For example, the resulting coupler can be more easily refined (especially at lower temperatures) At the temperature, it can also have a more uniform and more uniform charging characteristics. It can also be produced, and it can be further purified by the king of the ▲ method. For example, the chemical toner composition prepared by the above method is used to remove no, by-products or impurities and then dried. The chemical toning #iM compound of the present invention may further comprise an optional additive, 149104 .doc -24- 201120148 T can be optionally added Mixed or blended for the preparation of such compositions - or: a group of injuries will be explained in more detail below. Examples include carrier addition of hydrazine, positive or negative charge control agents (eg quaternary ammonium salts ... than biting salt) , sulphate, sulphate and citrate), flow aid (1), w'id addltive), lycopene or soil (for example, commercially available polypropylene and polyethylene). Chemical toner composition _+进# comprises iron oxide, wherein the iron oxide may be a magnetic carrier. The composition of the agent becomes a magnetic toner composition. Typically, the additives are in an amount of from about 0.05% by weight to about 3% by weight. However, smaller or larger amounts of additives can be selected depending on the particular system and desired properties. Machie has found that polymer modified pigments can be used to prepare chemical toner compositions having good overall properties. The polymer is modified, the pigment comprises a reaction product or a combination product of the modified pigment and the polymer, and the modified pigment comprises a pigment to which at least one organic group is attached, the organic group progress comprising at least one first functional group Base polymer There are fewer second functional groups. As described above, the chemical toner is prepared by dispersing the colorant in a medium such as a solvent and combining it with a resin or resin precursor dispersion or solution. Forming a chemical toner in which the coloring agent is well dispersed in the resin, the coloring agent must be dispersible in the medium and compatible with the system of the sputum, the tree sap and the tree sap. In addition, it must be formed in the formation of the chemical toner Maintaining good dispersion. It is expected that even if the pigment modified by the polymer can be well dispersed in the medium and thus with the height of the medium (4), the same pigment modified by the polymer may not be easily dispersed in the resin and "Valley" is included in the formation of the final chemical toner. Alternatively, even if the pigment modified by 149104.doc -25· 201120148 can be easily dispersed in the resin, it is expected that the same pigment may not be easily dispersed. In the medium. It has been found that, in particular, the dispersibility in the medium and the resin can be improved as compared to a chemical toner prepared from a pigment which does not contain a linking polymer group (and thus is not a polymer-modified pigment). A chemical toner that has overall properties, including improved hue, chroma, and/or image density. Although not wishing to be bound by theory, the properties of the surface modified pigment used to incorporate at least one embodiment of the chemical toner method consistent with the present disclosure may include the following. First, the modified pigment can be dispersed in an organic solvent', for example, to a primary aggregate size (<200 nm). The pigment dispersion should also be capable of being dropped into the bulk resin system in the solvent without flocculation or sinking. This host resin system can include other additive entities such as ruthenium and charge control. For example, the surface modified pigment can be directly dispersed in a mixture of the toner resin in ethyl acetate. Herein, the bulk toner resin may include a series of low-butyl polymers suitable for toner treatment (for example, but not limited to, 40-80t, for example, 5〇_7〇β〇, which includes 2 vinegar, styrene acrylic acid Lines, etc. After the modified pigment is incorporated into the host resin in the solution: the modified pigments can withstand a variety of adjustments: forming processing conditions, which can include the text "degree of expertise. At all In these steps, the modified pigment is kept well dispersed, and during the toner emulsification step: in the aqueous phase, 'the pigment is not present in the toner particles after the toner is formed. During the period, no pigment migrates to the interface, etc. Prepare 'condensation 149104.doc • 26- 201120148 The following are some examples 0 consistent with at least one embodiment of the present disclosure. Example 1. Acid/alkali method A. Polymer modified pigment Preparation: Add 1 〇g Amberlite IRN-77 Acidic Ion Exchange Resin (Supelco) to 1009 g of 10_00% solid Cab-O-Jet® 260M (pure urethane sulfonic acid treated Pigment Red 122) and use a simple top Mixing the contents for 24 hours. 24 small Afterwards, the ion exchange resin was removed using a Gerson 2000TM fine mesh (190 μm) coating filter. Then an average molecular weight of 37.8 g was added to the acidified Cab_〇_Jet® 260M viscous slurry to be about 2, Ρ0/Ε0 Mo The monoamine primary amine polyetheramine copolymer (Jeffamine® M-2070, Huntsman LLC) having an ear ratio of 1 0/3 1 of propylene oxide/ethylene oxide was stirred for an additional 24 hours using an overhead stirrer. After 24 hours, the thick slurry was placed in a heat-resistant glass dish and dried at 70 ° C for 1-2 days. After drying, the crude material was ground to a fine powder using a commercial coffee grinder. B. Preparation of the dispersion ( The polymer and the modified pigment red 122 (acid form) of Skandex grinding): metered in a 25 0 ml stainless steel paint can, 13 75 g including a purple-red pigment ion-exchanged with a sulfonic acid group (pigment red 122 , Sun Chemical) and Jeffamine M_2070 polymer polymer modified pigment and 36.25 g ethyl acetate as solvent. 6 〇g 2 claw glass beads were added thereto and mixed by mixing on a Skandex mixer for 6 hours. The dispersion is obtained. The resulting dispersion is extremely easy. Movable and can be easily filtered. Gers〇n 2000TM using fine mesh (190 microns) coatings filter glass beads were removed using 149104.doc • 27- 201120148

The Microtrac® Particle Size Analyzer measures the average volume particle size (mV) of the particulate matter in the dispersion and measures 〇. 12 1 μηι, 0.109 μηι d50, 0.229 μπι d95. C. Preparation of the Ding Liquid: The Jeffamine M was replaced by a procedure similar to that detailed in Example 1B and with a polyetheramine (Jeffamine M-2005) having a nominal molecular weight of 2000 and a PO/EO ratio of about 29/6. -2070, using Microtrac® particle size analyzer to measure the average volume particle size (mV) of the particulate matter in the dispersion and measured to be 0_132 μηι, 0.118 μηι d50, 0.247 μηη d95 ° D·Comparative example (conventional dispersant and not Skandex Grinding with Modified Pigment Red 122): 1 g of unmodified dry pigment red 122 (Sun Chemical, grade 228-8228), 9.375 g 40% active solids were metered into a 250 ml stainless steel paint can. Solsperse 32500 (Lubrizol) (3.75 g by dry weight) and 3 0.625 g of ethyl acetate were used as solvents. 6 g of g 2 mm glass beads were added thereto, and a dispersion was prepared by mixing on a Skandex mixer for 6 hours. The resulting dispersion is viscous and difficult to filter. Glass beads were removed using a Gers〇n 2000 tm fine mesh (19 μm) coating filter. The average volume particle size (mV) of the particulate matter in the dispersion was measured using a Micr® trac8 particle size analyzer and measured to be 0.320 μπι > 0.294 μηι d50 '0.566 μιη d95 ° 比较 · Comparative Example: Use and Example 1D A detailed procedure for the procedure is similar to the procedure using Jeffamine M-2005 instead of S〇lsperse 325〇〇, using the Micr〇trac8 particle size analyzer to measure the average volume fraction (mV) of the particulate matter in the dispersion and measure 149104.doc •28 · 201120148 was 1.131 μιη, 0.849 μηι d50, 2.785 μΐΏ d95 ° F. Comparative Example: Using a procedure similar to that detailed in Example 1E and replacing Mt 2070 with Jeffamine M-2005, using a Microtrac® particle size analyzer The average volume particle size (mV) of the particulate matter in the dispersion was measured and found to be 0.608 μηη, 0.475 μηι d50, 1.381 μιη d95 〇G. Comparative Example (surface modified pigment red 122 without acid dispersant) Form) Skandex Grinding): 10 g of metered addition in a 250 ml stainless steel paint can consist of ion exchange with an acidic resin followed by drying with a sulfonic acid group The surface of the magenta pigment was modified with a pigment (Pigment Red 122 'Sun Chemical) and 40 g of ethyl acetate as a solvent. 60 g of 2 mm glass beads were added thereto, and a dispersion was prepared by mixing on a Skandex mixer for 6 hours. The resulting dispersion is less dispersible and produces a highly viscous gel that is extremely difficult to filter. Glass beads were removed using a Gers〇n 2000TM fine mesh (190 micron) coating filter. The average volume fraction (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and the measurement was 1.291 μηι ' 1.269 μηι d50, 1.833 μηι d95. Η·Comparative example (Skandex grinding with modified pigment blue 15:4 in the absence of polymer dispersant (hydrophobic diazotide)): 1 〇g in 250 ml stainless steel paint cans including fluoroaniline attached The surface of the cyan pigment (phthalocyanine pigment blue 15:4) which was subjected to a pigment treatment at 1.5 mmol/g was subjected to a modified pigment and 4 g of ethyl acetate as a solvent. 60 g of 2 mm glass beads were added thereto, and a dispersion was prepared by mixing for 6 hours on a Skandex mixer at 149104.doc -29-201120148. The resulting dispersion is very viscous but becomes more fluid when sheared. The glass beads were removed using a Gerson 2000TM fine mesh (19 μm) coating filter. The average volume particle size (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and measured as 〇 596 pm, 0. 574 μηι d50, 0.816 μπι d95 〇 1. Preparation of the dispersion (polymer and Rotstated by a modified pigment red 122 (acid form): 15 g of a magenta pigment containing a sulfonic acid group (diazo treated) ion exchanged in a 250 ml glass beaker ( Pigment Red 122) A polymer modified pigment of Jeffamine M-2070 polymer and 85 g of ethyl acetate as a solvent. The dispersion was prepared by mixing IS min at 5000 rpm using an IKA® T25 digital ULTRA-TURRA® mixer. The resulting dispersion is extremely flowable and can be easily filtered. The glass beads were removed using a Gers〇n 2〇〇〇tm fine mesh (190 micron) paint filter. The average volume particle diameter (mV) of the particulate matter in the dispersion was measured using a Micr〇trac@ particle size analyzer and found to be 0.133 μηι, 0.126 μηι d50, 0.230 μπι d95. J. Comparative example (conventional dispersant mixed with unmodified pigment red 122 rotor): Add 1 〇g unmodified dry pigment red 122 in a 250 ml glass beaker (Sun Chemical' grade 228 -8228) and a dry mixture of Solsperse 32500 (Lubrizol) in the same amount as Example π and 73 66 g of ethyl acetate 9 were prepared by mixing at 5000 rpm for 15 min using an IKA® T25 digital ULTRA-TURRA® mixer. The resulting dispersion was poorly dispersible'. Most of the dry pigment settled to the bottom of the beaker when it was left standing. Use 149104.doc -30- 201120148

Gerson 2000TM fine mesh (190 micron) paint filter removes glass beads. The average volume fraction (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and found to be 0.774 μηη, 0.478 μηι d50, 4.5 1 μΓη d95 ° Example 2. APSES Method · Polymer Modification Preparation of the pigment: In the Ross mixer, add 6000 g of deionized water (at a concentration of 20 ° / solids) to the boo with 乞 :: 3 (phthalocyanine, Cladant toner grade, batch number DEBF009196). in). To this mixture was added 422 g of sulfonic acid aminophenyl sulfone ethyl ester (APSES, 1 mmol/g pigment) and the reaction mixture was brought to 60 °C. 1 〇 3 5 g of sodium nitrite 〇 mmol / g of pigment) was slowly added to the reaction mixture. The reaction was allowed to proceed for 2 to 4 hours. The crude APSES treated PB® 5:3 is then divided into two equal portions, where the first portion (crude) will remain in the crude state throughout the subsequent polymer attachment pathway and the second portion (diafiltration filtered) will be subjected to diafiltration. To remove any unreacted starting materials and salts. The second apses-modified APSES-PB:13 dispersion in water was subjected to diafiltration with deionized water to achieve a target osmotic conductivity of <25 〇y/cm and then concentrated to 14 39%. The final solid was cleaned with APSES modified PB 15:3 (diafiltration once). The final solid was found to be 13.69% in the crude APSES modified pB 15:3 from the first (crude). 77.0 g of amine M-2070 was added to a crude APSES-modified PB15_3 pigment (crude 'from above) dispersion in 1500 g of 13.69% solids in water. The pH of the mixture was adjusted to 2.5 149104.doc 201120148 with sodium hydroxide and allowed to react for 24 hours by means of an overhead stirrer. In the first example, the crude mixture was dried overnight at 70 ° C to obtain a crude APSES PB 15:3 (sample A1) treated with Jeffamine M-2070. In the second example, the pH of the crude Jeffamine M-2070 APSES PB 15:3 was adjusted to pH 10 with hydrochloric acid, followed by dialysis to remove any unreacted polymer and salt. The APSES-PB:13 dispersion modified with jeffaniine m-2070 in water was then dialyzed against deionized water to achieve a target penetration conductivity of <25 〇 gs/cm. The clean dispersion was then dried overnight at 7 ° C to obtain APSES PB 15:3 (Sample A2) treated with Jeffamine M-2070. The solution was stored at 14.2 2 _ 4 g with 14.3 % solids. 66.0 g of Jeffamine M-2070 was added to the APSES treated PB1 5:3 pigment (diafiltration filtered, from above) diafiltration filtered in water. The pH of the mixture was adjusted to 12.5 with sodium hydroxide and allowed to react for 24 hours by means of an overhead stirrer. The first mixture was dried overnight at 70 ° C to obtain APSES PB 1 5:3 (Sample B1) treated with Jeffamine M-2070. The pH of the second Jeffamine M-2070 APSES PB15:3 was adjusted to pH 10 with hydrochloric acid, followed by diafiltration with deionized water to achieve a target permeation conductivity of <250 gs/s/cm to remove any unreacted polymerization. And salt. The clean dispersion was dried overnight at 70 ° C to obtain APSES PB 15:3 (sample B2) treated with Jeffamine M-2070. B. Preparation of Dispersion (Skandex Grinding of APSES-treated Pigment Blue 15:3 (Sample B2) by Polymer Modification): 13.75 g was metered in 250 ml stainless steel paint cans and dialyzed twice 149104. Doc -32- 201120148; APSES-treated pigment blue 1 5 3 (sample B modified by Jeffamine M-2070 after human APSES diazonium reaction and once after jeffarnine M-2070 polymer linkage) 2) and 3 6.2 5 g of ethyl acetate are intended as solvents. 60 g of 2 mm glass beads were added thereto, and a dispersion was prepared by mixing on a Skandex mixer for 6 hours. The resulting dispersion is extremely fluid and can be easily handled. Glass beads were removed using a Gerson 2000TM fine mesh (190 micron) paint transitioner. The average volume fraction (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and measured as 241·241 μηι, 213 213 μηι d50, 0.476 μηι d95. Preparation of C* Dispersion: (Skandex Grinding of APSES Treated Pigment Blue 15:3 (Sample B1) by Polymer Modification) Using procedures similar to those detailed in Example 2B and only at APSES After the connection step, the APSES-treated pigment blue 15:3 modified by Jeffamine m_2〇7〇 was dialyzed (sample was used instead, and the average volume particle size of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer ( mV) and measured as 0.176 μΓη, 〇165 μΙΏ d50, 0.295 μηι d95 ° D. Preparation of the dispersion: (polymer-modified APSES-treated pigment blue 15:3 (s model A2) Skandex mill) APSES-treated pigment blue 15:3 (sample a2) modified with Jeffaniine m-2070, diafiltered only after the Jeffamine M-2070 ligation step, was used instead of the procedure similar to the procedure detailed in Example 2C. The average volume particle size (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and found to be 0 322 μηι '0.294 μιη d50, 0.575 μιη 149104.doc -33- 201120148 d95. E. Dispersion Preparation: (APSES treated with polymer modification Pigment Blue 15:3 (Sample A1) Skandex Milling APSES treated pigment modified with Jeffamine M-2070 using a procedure similar to that detailed in Example 2D and completely diafiltration-free filtration Blue 15:3 (sample A1) was used instead, and the average volume fraction (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and measured to be 0.291 μηι, 0.228 μηι d5 0, 〇·735 μπι d95 〇F. Comparative example (conventional dispersant or polymer with unmodified pigment blue enamel 5:3 Skandex grinding): Measured 丨〇g unmodified dry pigment blue in 250 ml unrecorded steel paint can 15:3 (Sun Chemical 'grade number 24094-84), 9.375 g of 40% active solid Solsperse 32500 (Lubrizol) (3.75 g by dry weight) and 30.625 g of ethyl acetate as solvent. 6 〇g 2 was added thereto. Mm glass beads, and the dispersion was prepared by mixing on a Skandex mixer for 6 hours. It was passed as a viscous viscous and difficult to transition. Gerson 2000TM fine mesh 〇 9 〇Ί 米 ) 涂料 ; ; ; ; ; ; glass bead. The average volume particle diameter (mv) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and found to be 0.861 μm, 0.620 μηι d50, 2.655 μmη d95. Example 3. Thermal condensation method A. Preparation of polymer modified pigment (C1): PABA-treated carbon black was prepared by reacting p-aminobenzoic acid (PABA) with stoichiometric amount. Sodium nitrite reacts to form a diazonium salt, which is then reacted with a Regal® 330 (R33®) pigment (Cab〇t 149104.doc -34-201120148) to produce a PABA-treated pigment. 50 g dry PABA-treated R33 质 (protonated acid form), 25 g using an overhead stirrer

Stir the Jeffamine M-2005 and 600 g of deionized water for 3 〇 min. After 3 〇 min, the mixture was placed in a heat-resistant glass dish and dried overnight at 丨65 °C. The crude material was stirred in a large stainless steel beaker containing 1500 g of deionized water. The pH of the slurry was then adjusted to pH 2 and the slurry was mixed for 1-2 hours. After mixing for 1-2 hours, the carbon black slurry was filtered and washed with an additional volume of water until the pH of the wash water was pH > After adjusting the pH, the treated carbon black (sample ci) was placed in a heat-resistant glass dish and dried at 7 (rc for 1 to 2 days). The thermogravimetric analysis (TGA) of the polymer-modified carbon black obtained indicates the first time. The polymer connectivity after acid washing was 23.44% (TGA indicates 20.76% after the second acid wash) 〇B. Comparative example (C2):

50 g of the dry PABA treated R3 30 (protonated acid form), 25 g of Jeffamine M-2005 and 600 g of deionized water as in Example 3 A above was stirred using an overhead stirrer for 30 min. After 30 min, the mixture was placed in a heat resistant glass dish at 70. (: dry overnight. Then stir the crude material in a large steel beaker containing [500 g deionized water. Then adjust the pH of the slurry to pH 2 and mix the decomposed liquid for 1 _2 hours. After mixing for 1 _2 hours The transition carbon black slurry was washed with an additional volume of water until the pH of the wash water was > 4. After the pH was adjusted, the treated carbon black (sample C2) was placed in a heat-resistant glass dish and dried at 7 ° C. 2 days. Thermogravimetric analysis (TGA) of the resulting polymer modified carbon black showed a polymer connectivity of 765% after the initial acid wash (tga indicates 6.77% after the second acid wash). .doc •35- 201120148 C. Preparation of dispersion (Cld) (Skandex grinding of R330 modified by Jeffamine M-2005 (thermal condensation at 165 ° c, sample: metered in 250 ml stainless steel paint cans 13 〇62 g (polymer connectivity: 23.44%. 1 〇g pigment) at 165 (R heat condensation of Jeffamine M-2005 modified R330 (sample Cl) and 36.93 g of ethyl acetate as solvent) 60 g of 2 mm glass beads were added thereto, and a dispersion was prepared by mixing on a skandex mixer for 6 hours. It is easy to flow and can be easily filtered. The glass beads are removed using a Gerson 2000TM fine mesh (190 micron) paint transitioner. The average volume fraction (mV) of the particulate matter in the dispersion is measured using a Microtrac® particle size analyzer and measured.得 147 μηι, 0.139 μηι d50, 0.226 μηη d95. D·Comparative Example (C2d) (dispersed by Skandex grinding of R330 (thermal condensation at 70 C, sample C2) modified by Jeffamine M-2005) Liquid): 1330 g (polymer connectivity 7.65 °/., 10 g pigment) is thermally condensed in a 250 ml uncoated steel coating tank by jeffamine M_2005 modified R330 at 7 °C (Sample C2) and 39.17 g of ethyl acetate as a solvent, 60 g of 2 mm glass beads were added thereto, and the dispersion obtained by mixing on a skandex mixer for 6 hours was extremely viscous and difficult to filter. The glass beads were removed using a Gerson 2000TM fine mesh (19 μm) coating filter. The average volume fraction (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and measured to be 0.545 μηιη, 〇359 μπι d5 〇, 1.606 μηι d95 Example 4. Ion-dipole method (similar procedure to acid/base method) 149104.doc •36· 201120148 A. Preparation of modified pigment (Dl): at 927 § 10.00% solid €& 15-0- Add 1.5 g of Amberlite IRN-77 Acidic Ion Exchange Resin (Supelco) to ^1@ 270 丫 (by Aminobenzenesulfonic Acid Treated Pigment Yellow 74 'Na+ Form) and stir the contents for 24 hours using simple overhead mixing . After 24 h, the ion exchange resin was removed using a Gerson 2000TM fine mesh (190 micron) coating filter. The viscous slurry was then placed in a heat-resistant glass dish and dried at 70 ° C for 1-2 days. After drying, the crude treated pigment was ground to a fine powder using a commercially available coffee grinder to obtain a pigment yellow 74 (H+ form) treated with p-aminobenzenesulfonic acid. B. Preparation of Modified Pigment (D2>: Amberlite IRN-77 Acidic Plantation (Supelco) was replaced with Dowex Monosphere 99Ca/320 (calcium ion exchange resin) using a procedure similar to that described in detail in Example 4A. Preparation of aminobenzoic acid-treated pigment yellow 74 (Ca++ form) C. Preparation of modified pigment (D3): at 994 g 1〇% solid Cab_〇_Jet® 27〇γ dispersion 9.4 g of ZnCh was added to the company (Cab〇t) and the mixture was stirred overnight using a simple overhead mixing method. The sample was centrifuged at 4100 rpm for 30 min and the supernatant was decanted. Deionized water was added to the crude centrifugal pigment cake. The centrifugal cleaning procedure was repeated until the supernatant had a conductivity of <500 pS/cm after centrifugation. The crude pigment cake was then placed in a heat-resistant glass dish and dried at 7 (TC for 1-2 days. After drying, a commercial coffee mill was used. The crude treated pigment is milled into a fine powder to obtain a pigment yellow 74 (Zn++ form) treated with p-aminobenzenesulfonic acid. D. Preparation of modified pigment (D4): 149104.doc -37- 201120148 A program similar to the one described in detail in Example 4C

Substituting ZnCl2 for CuCl2, pigment yellow 74 (Cu++ form) treated with p-aminobenzenesulfonic acid was obtained. Preparation of 分散·Dispersion (Polymer and Skandex Grinding with Modified Pigment Yellow 74 (Cu++ Form, since D4)): Add 10 g of modified amine-based acid in 250 ml stainless steel paint can. Pigment Yellow 74 (Cu++ Counterion, Sample D4), 3.75 g

Jeffamine M-2070 and 36.250 g of ethyl acetate were used as solvents. 60 g of 2 mm glass beads were added thereto and a dispersion was prepared by mixing on a Skandex mixer for 6 hours. The resulting dispersion is extremely flowable and can be easily filtered. Glass beads were removed using a Gerson 2000TM fine mesh (1 90 micron) paint filter. The average volume particle diameter (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and found to be 0.1551 μm, 0.1428 μπι d50, 0.2851 μm d95. A similar procedure was carried out for the p-aminobenzenesulfonic acid treated ΡΥ74 with Η+, Na+, Ca++ and Ζη++ counterions (see table below) 0 Counterionic polymer Mv (μηι) 50% (μηι) 95% ( Ηηι) H+ None 0.726 0.692 1.152 H+ Jeffamine M-2070 0.1434 0.1388 0.2437 Na10 No 1.519 1.172 3.69 Na+ Jeffamine M-2070 1.733 1.724 2.116 Ca++ No 1.201 1.119 1.938 Ca++ Jeffamine M-2070 1.159 1.082 2.430 Zn++ Jeffamine M-2070 0.1406 0.1357 0.2462 Cu++ No 1.284 1.176 2.518 Cu++ Jeffamine M-2070 0.1551 0.1428 0.2851 F. Comparative Example D5 (Skandex grinding of surface modified pigment 149104.doc -38 * 201120148 Page 74 (PY74) (Cu++ form) without polymer dispersant ): 1 〇g of pigment yellow 74 (Cu++ counterion) modified with amino benzene sulfonic acid and 40 g of ethyl acetate were metered in a 250 ml stainless steel paint can. 60 g of 2 mm glass beads were added thereto, and a dispersion was prepared by mixing in a Skandex mixed state for 6 hours. The resulting dispersion was thick and difficult to filter. Glass beads were removed using a Gerson 2000TM fine mesh (19 μm) coating filter. The average volume fraction (mV) of the particulate matter in the dispersion was measured using a Microtrac® particle size analyzer and measured to be 1 284 μΓη, 1.176 μηι d50, 2.518 μπι d95. Example 5. Direct Diazo Connection of Polymer A. Preparation of Polymer Modified Pigment (E1): Add 50 g of R330 to a 500 g ethanol/water (50/50) mixed solution and use simple overhead mixing Stir in the method. Add 56.4 g of Jeffamine XTJ 623 (an aniline-terminated analog of Jeffamine M-2005 '0.564 mmol/g R330=28.2 mmol) to 200 g ethanol/water (5 0/50) in a separate 5 〇〇mi glass beaker Mix the solution and mix on a stir plate. Then 2 ml of methanesulfonic acid (31 mmol) was added to the solution and after stirring for 15 min with the acid, 1.95 g of sodium nitrite (28.2 mmol) was slowly added to the solution to partially convert the aniline to the diazonium salt. After 15 min of mixing, the diazonium salt of Jeffamine XTJ 623 was slowly added to the R33 mash slurry in ethanol/water (5 〇/5 Torr). The reaction was allowed to proceed at room temperature for 2 hours. After 2 hours, the dispersion in ethanol/water was placed in a heat-resistant glass dish and dried overnight at 10 (TC). The next day, the crude material was stirred in a large stainless steel beaker containing 1500 g of deionized water. The pH is adjusted to pH 2 and the slurry is mixed 1-2 149104.doc •39· 201120148 hours. After mixing for 1-2 hours, 'filter the carbon black slurry and wash the sue with an additional volume of water until the pH of the washing water> 4 After adjusting the pH, the treated carbon black was placed in a heat-resistant glass dish and dried at 7 Torr. (: drying for 1-2 days. Thermogravimetric analysis (TGA) of the resulting polymer-modified carbon black showed initial acid washing. Post-polymer connectivity is 36.29%. Preparation of B* dispersion (Skandex milled with Jeffamine XTJ 623 modified R330, diazo connection): 13 〇 62 g (polymer connection) in 250 ml stainless steel paint cans The degree of 23_44%, 1〇g pigment) is a heat-condensed solvent of R33〇 and 36.93 g of ethyl acetate modified by 打(10) M-2005 (diazo-linked jeffamine XTJ 623). Add 6〇g 2 melon-claw glass beads and mix them on the Skandex mixer The dispersion was prepared in 6 hours. The resulting dispersion was extremely flowable and easily filtered. The glass beads were removed using a Gers〇n 2〇〇〇1 fine mesh (190 μm) coating filter. The average volume particle size (mV) of the particulate matter in the dispersion was measured and measured to be 0.112 μηι, 0.1046 μηι d50, 0.171 μιη d95. Coloring properties: Except for the pseudo-colloid stability test (eg, particle size, viscosity, etc.) The coloring properties of carbon black and color pigment dispersions in ethyl acetate and polyester resins (Reich〇M Fme-T_T-6694 resin) were also evaluated. For example, Reichold Fine-Tone T_6694 resin and a stock solution of the pigment dispersion in ethyl acetate and blended with a pigment loading from 1% to 6% pigment/resin ratio. Then use a 2 mil (〇〇〇 2 inch micron) drawdown bar The resulting formulation was applied to a BYK_Gardner opaque card 149104.doc 201120148. The color performance of the resulting film was then analyzed using a HunterLab spectrophotometer and the results are illustrated in Figures 1-4. Prepared from Jeffamine M-2070 APSES PR122 The film exhibited better color rendering properties than the unmodified pRl22 sample with the conventional dispersant Solsperse 325 00. As generally illustrated in Figure 1, the polymer is directly attached to the pigment surface at a lower % pigment loading. Produces a large chromaticity value. The point "" represented by the square indicates the data point of the pigment-modified pigment of Jeffamine M-2070 APSES PR_ m, and the point "▲" represented by the triangle indicates the data point of the unmodified PR122 of Solsperse 32500. In addition to improving the chromaticity, the direct connection of the polymer to the surface of the pigment can also improve the color gamut' as illustrated generally in Figure 2. Jeffamjne M-2070 APSES_PH 122 Fuchsia Dispersion (data points shown in square "") can achieve a warmer shade of purple (yellow hue), which is a conventional dispersant (eg unmodified PR122 with Solsperse 32500) (It is impossible to use the data point shown by the triangle "▲"). Turning now to Figure 3, similar to the results observed with PR122, jeffamine M-2070 APSES PB15:3 (samples Bl, B2, and A1) cyan dispersions are able to achieve the most neutral hue of cyan (ignoring a* contribution) The color gamut can be improved, which is not possible with the unmodified PB 15:3 dispersion containing Solsperse 32500. In Fig. 3, the data point of the sample B1 is represented by a diamond "♦"; the data point of the sample B2 is represented by a triangle r ▲"; and the data point of the sample A is represented by "X". The data points of PB 15:3 and jeffamine M-2070 (p-aminobenzoic acid) linked in a non-covalent manner are represented by a circle "·". With 149104.doc 41 _ 201120148

Solsperw 32500's unmodified pb 15:3 data point is the same as PR 122 pigment by square "" for 'polymer' and pigment directly connected to provide matching unmodified PB at lower % pigment loading 15:3 S〇isperse 32500 is the ability to disperse the chromaticity value. For example, the jeffamine APSES PB15:3 (B2) cyan dispersion has similar coloring properties at 4% pigment with an unmodified pb 15:3 dispersion containing s〇lsperse 32500 at 6% pigment loading. Therefore, the jeffamine M-2070 APSES PB15.3 (B2) cyan dispersion allows the toner to achieve the same coloring performance with less than 2% pigment. 0 As illustrated in Figure 4, it has been found to be conventionally dispersed with unmodified ργ74 32500. Compared with the sample (triangle, "▲"), Jeffamine M_2070 (p-amino sulfonate) ργ74 dispersion ("square""), which is combined in a non-covalent manner, is shown in the pigment loading range (2_6% pigment). The significant chroma of the near soap level is improved to produce a brighter, more fresh film. Resin compatibility: In addition to the standard colloidal stability test and color performance test, the surface modified carbon black and color pigment and the main polyester resin

The compatibility between Fine_T_ Τ·6694 resin) was evaluated. For example, a stock solution of Reich〇ld Fine_T_ state resin and pigment dispersion in ethyl acetate was prepared and formulated at a pigment/resin ratio of 1%. After using the _ stick ((4), micron), the obtained formulation was scraped on a glass microscope slide 1 and then the light (4) micro-optical microscope was used to analyze the uniformity of the obtained film and the compatibility of the film:: The compatibility results of the modified +μ + υ 丞 枓 枓 枓 枓 枓 枓 枓 枓 枓 枓 枓 枓 枓 枓 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 149 For example, 'Figure 5 illustrates Regai 330_ p-aminobenzenesulfonic acid (acid form) and Jeffamine M-2070 (1% polymer modified pigment in Reichold Fine Tone T-6694 polyester resin) Compatibility results. For example, 'Figure 6 illustrates the compatibility results of Pigment Blue 15:4-APSES-Jeffamine M-2070 (1% polymer modified pigment in Reichold Fine Tone T-6694 Poly S resin) . For example, Figure 7 illustrates the compatibility results for Pigment Red PRUZ-APSES-Jeffamine M_2005 (1% polymer modified pigment in Reichold Fine Tone T-6694 polyester resin). For example, Figure 8 illustrates the compatibility results for Pigment Yellow 74-APSES-Jeffamine M-2005 (1% polymer modified pigment in Reich〇ld Fine Tone T-6694 polyester resin). For example, Figure 9 illustrates Regal 330-p-aminobenzoic acid (acid form) thermally condensed with jeffamine M-2005 (165 ° C) (1% in Reichold Fine Tone T-6694 polyester resin) The result of compatibility of the polymer modified pigment). For example, 'Figure 10 illustrates Regal 330-p-aminobenzoic acid (acid form) thermally condensed with jeffamine M-2070 (165 ° C) (1% in Reichold Fine Tone T-6694 polyester resin) The result of compatibility of the polymer modified pigment). For example, 'Figure 11 illustrates the phase of R330 (direct diazo connection) modified by jeffamine XTJ 623 (1% polymer modified pigment in Reich〇id Fine Tone T-6694 polyester resin) Capacitive results. 149104.doc 43. 201120148 Contrary 'Figure 12-14 illustrates a comparative example. For example, Figure 2 illustrates an untreated pigment red 122 with a conventional dispersant (Solsperse 32500-Lubrizol) (1% polymer modified pigment in Reichold Fine Tone T-6694 polymer resin) A comparative example of the compatibility results. Figure 13 is a diagram showing untreated Pigment Blue 15:4 and styrene-acrylic copolymer (Joncryl 586-BASF polymer) (2 in Reich〇ld Fine T〇ne T-6694 polyester resin) A comparative example of the compatibility results of % polymer modified pigments. Figure 14 is a diagram illustrating thermal condensation with jeffamine M_2〇〇5 (7 〇β〇 of Regal 33〇-p-aminobenzoic acid (acid form) (stored in Reich〇id FiM Tone T-6694 polyester resin) A comparative example of the compatibility results of % polymer modified pigments. A pigmented formulation modified in a polymeric manner in accordance with an embodiment of the present disclosure (eg, 'Fig. 5-(1) is displayed in a polys. Good overall compatibility. In all cases, the polymer modified surface rough &amp; negative &lt; 顋枓 is well dispersed and not coalesced. The comparison with the conventional dispersant test is a simple example (for example , Figure 12-14) shows poor dispersibility in the polyester film, such as by the large agglomerate in the case of you, and the dispersion of the 丨 weight difference in ethyl acetate alone, where particle size &gt; 3 nm. Conversely, it has been shown that the polymer-stabilized pigments in accordance with the disclosure of this issue have excellent &quot;good dispersion properties alone (for example, granules &lt; 2 ϋ 0 nm). The purpose has been to implement the above instructions for this ice / 1 &lt; drought and good. This article is not intended to pack The invention is limited to the disclosed form of 149104.doc • 44 - 201120148. In light of the above teachings, various modifications and variations are possible and may be obtained from the practice of the invention. Modifications and variations of the embodiments of the present invention are intended to be illustrative of the principles of the present invention and its application, so that those skilled in the <RTIgt; The scope of the present invention is intended to be defined by the scope of the accompanying claims and their equivalents. FIG. 1 to 4 illustrate at least one embodiment consistent with the present disclosure. Coloring properties of various chemically prepared toner compositions; Figures 5 through 1 1 illustrate compatibility results for various chemically prepared toner compositions consistent with at least one embodiment of the present disclosure; And Figures 12 through 14 illustrate the compatibility results for various comparative examples. 149104.doc •45·

Claims (1)

201120148 VII. Patent Application Range: 1 . A chemical toner composition comprising a resin and a polymer-modified pigment comprising a pigment to which at least one polymerizable group is attached, wherein the pigment modified by the t5 substance comprises The reaction product of the following substance a) comprises a modified pigment comprising a pigment having at least one organic group, wherein the organic group comprises at least one first functional group, and b) at least one polymerization comprising at least one second functional group And wherein the first functional group of the modified pigment reacts with the second functional group of the polymer to form the polymer-modified pigment. 2. The chemical toner composition of claim 1, wherein 0 the first functional group of the modified pigment is an electrophilic group and the second functional group of the polymer is a nucleophilic group, or 11) The first functional group of the modified pigment is a nucleophilic group and the second functional group of the polymer is an electrophilic group. 3. The chemical toner composition of claim 2, wherein the first functional group of the modified pigment is an electrophilic group and the second functional group of the polymer is a nucleophilic group. 4. The chemical toner composition of claim 2, wherein the first functional group of the modified pigment is a nucleophilic group and the second functional group of the polymer is an electrophilic group. 5. The chemical toner composition of claim 2, wherein the first functional group of the modified pigment and the second functional group of the polymer are independently selected from the group consisting of: a carboxylic acid; an ester; an acid Gas; sulfonium gas; hydrazine azide; isocyanic acid vinegar; _1; aldehyde; acid anhydride; decylamine; quinone imine; imine; α, β _ 149104.doc 201120148 and ketone, aldehyde or sulfone; Ii; epoxide; alkyl sulfonate or alkyl sulfate; aromatic compound capable of addition-elimination reaction; amine; hydrazine; alcohol; thiol; hydrazine; And its salts or derivatives. 6. The chemical toner composition of claim 2, wherein the first functional group of the modified pigment reacts with a second functional group of the polymer to form an addition between the modified pigment and the polymer Formation - elimination of products. 7. The chemical toner composition of claim 6, wherein the first functional group of the modified pigment is an alkyl sulfate group and the second functional group of the polymer is an amine group. 8. The chemical toner composition of claim 7, wherein the alkyl sulfate group is a (2. sulfate ethyl) sulfone group. 9. The chemical toner composition of claim 1, wherein the organic group is a phenyl-(2-sulfatoethyl)-sulfone group. 10. The chemical toner composition of claim 2, wherein the first functional group of the modified pigment reacts with a second functional group of the polymer to form a boundary between the modified pigment and the polymer Condensation product. 11 ', as in June, the chemical toner composition of the present invention, wherein the first functional group of the modified pigment is an amine group and the second functional group of the polymer is a carboxylic acid group ' and wherein the condensation The product is decylamine. 12. The chemical toner composition of claim 1 , wherein the first functional group of the modified pigment is a carboxylic acid group and the second functional group of the polymer is an amine group and wherein the condensation product is Guanamine. 13. The chemical toner composition according to claim 1, wherein the modified pigment is 149104.doc 201120148 14 15. 16. 17. 18. 19. The arylenic alcohol group and the polymer The difunctional group is a slow acid group ' and wherein the condensation product is an ester. 'Chemical toner composition of the present invention, wherein the first functional group of the modified pigment is a carboxylic acid group and the second functional group of the polymer is an alcohol group' and wherein the condensation product Ester. The chemical toner composition of claim 1, wherein the first functional group anion or an anionizable earth group of the modified pigment and the second functional group cation or cationizable group of the fluorene polymer The group 'or X', 'the first functional group cation or the cationizable earth group and the second functional group anion or an anionizable group. A chemical toner composition of the first aspect of the invention, wherein the first functional group of the modified pigment is cationizable and the second functional group of the polymer is anionizable. The chemical toner composition of claim 15 wherein the modified genomic group of the modified pigment is anionizable and the second functional group of the polymer is 1% ionizable. The chemical toner composition of claim 15, wherein the g energy group of the modified pigment reacts with the second functional group of the polymer to form a salt between the modified pigment and the polymer. The chemical toner composition of claim 18, wherein the S-energy group of the modified pigment is a sulfonic acid ruthenium or a carboxylic acid group and the second functional group of the polymer is an amine group, and wherein Salt ammonium salt. 20. The chemical toner composition of claim 18, wherein the modified &lt;RTI ID=0.0&gt;&gt;&gt;&gt;&gt; An acid group, and wherein the salt is an ammonium salt. 21. The chemical toner composition of the present invention, wherein the polymer is an amine terminated polymer. 22. A chemical toner composition according to the formula, wherein the polymer is an amine terminated polyalkylene oxide. * 23. The chemical toner composition of claim </RTI> wherein the polymer is a resin. 24. A chemical toner composition comprising a resin and a polymer-modified pigment comprising a pigment to which at least one polymeric group is attached, wherein the polys-modified pigment comprises a combination of the following: a) a modified pigment comprising a pigment to which at least one inherent organic group is attached, wherein the organic group comprises at least one first functional group, and b) at least one polymer comprising at least one second functional group, wherein The first functional group of the modified pigment and the second functional group of the polymer coordinate with each other to form the polymer modified pigment and wherein i) the functional group anionic group of the modified pigment And the second functional group of the polymer is a cationizable group, or 第) the first functional group of the modified pigment is a taucation group and the second functional group of the polymer is an anionic group. The chemical toner composition of claim 24, wherein the first functional group of the modified pigment is coordinated to the second functional group of the polymer to form a boundary between the modified pigment and the polymer. Association ion pair. 149104.doc -4- 201120148 26. 27. 28. 29. 30. 31. 32. 33. 34. The chemical toner composition of claim 24, wherein the conjugated functional group of the modified pigment is continued An acid salt group and a second functional group amine of the polymer wherein the acid salt group has K+, Li+, Cs+, Ca+2, and the chemical toner composition of claim 24 has the formula -S〇 3_M+ 'where M+ is Na+, Cu+2, Zn+2, Fe+2, Fe, Zr". A toner composition wherein the polymer amine is encapsulated as the chemical _ terminal polymer of claim 24. The condensed polycyclodecane of claim 24. The lipid of claim 24, wherein the polymer is an amine-based toner composition, wherein the polymer is a chemical toner combination And a polymer-modified pigment comprising a pigment to which at least one polymeric group is attached, wherein the poly-group has the formula _X_z_[Pa〇]_r, wherein directly connected to the X of the pigment a aryl or heteroaryl group; z series NR, or R and R, Η, C1-C18 alkyl 'C1_C18 fluorenyl, aralkyl, alkaryl or aryl; a group of H, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group, such as the chemical toner composition of claim 3, wherein X is an aromatic A chemical toner composition according to the item 5, wherein the pao is a copolymer of oxime and propylene oxide. The chemical toner composition of claim 3, wherein the z is NH 149104.doc